


And Where is That Supposed to Go?

by NaughtyPastryChef



Series: Orgasms For Everyone! spn Kinktober 2017 [16]
Category: Supernatural
Genre: Anal Fingering, Anal Sex, F/M, First Time, Pegging, Rimming, Sex Toys
Language: English
Status: Completed
Published: 2017-10-17
Updated: 2017-10-17
Packaged: 2019-01-18 11:29:18
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 747
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12387183
Author URL: https://archiveofourown.org/users/NaughtyPastryChef/pseuds/NaughtyPastryChef
Summary: kinktober day 16 prompt: Pegging. Sam has taken to all the anal play so far, so Jess thinks it's time to step up her game.





	And Where is That Supposed to Go?

[Jess' Inspiration](https://www.pinkcherry.com/fetish-fantasy-vibrating-strap-on-set-1)

 

“And where do you think that’s going to go? Is this some kind of kinky dp fantasy you’ve got? Cause I dunno if I can wear that thing and fuck both your holes at once.” Sam says, staring at the six inch black dildo in Jess’ hand. “I’m not saying I don’t wanna try that, but it sounds like a lot of work.” He lays back on the bed and puts his arm behind his head as she laughs at him. Her laughter is infectious and soon he’s laughing along with her even though he’s certain that he doesn’t get the joke.

“It’s for you. Baby’s first pegging.” She smiles and waves it in his face ridiculously and he stops laughing abruptly.

“Look, Sam, I know you’re new to all the ass play, but you’ve liked it all so far, haven’t you? Fingers and tongue? This is just the next thing to try.” She tries to reason with him but he’s frozen. 

It’s one thing to think it’s hot that your gorgeous girlfriend wants to eat out your ass, and yeah, it’s one of the most amazing things he’s ever felt, but this seems different. Bigger.

“If you don’t want to…” She trails off, some of the joy leaving her eyes.

“No, it’s not that it’s just… This is different than the rest of it. This is…” He’s searching for the words, his eyes unfocused.

“It’s your ass cherry, it’s a big deal. I get it.” She tosses the black silicone to the foot of the bed and curls her warm, naked body up to his. He pulls a few of her curls through his fingers again and again, still thinking.

“You really wanna?” He whispers into the top of her head and feels more than sees her nod.

“I think it’d be hot. You up on your hands and knees, squirming on the end of my black cock. I mean, who wouldn’t want to do that?” It’s a rhetorical question but there’s an answer on the tip of his tongue anyway and it’s not one she would want to hear. He ruthlessly shoves the thought aside, gripping her ass in one hand and rolling them, so she’s straddled across his lap.

In no time and yet an eon later, Sam finds himself panting into the pillow with his ass in the air. Jess had started with her tongue, clever girl, and gotten him all riled up. Then there were massive amounts of silicon lube and her fingers and a little more tongue. Sam was far removed from the boy with doubts from earlier; now he was gagging for it.

The first touch of the fake cock to his hole made him want to shy away, but Jess pressed her sweaty, naked breasts against his back and reached around to grips at his cock with her free hand. She held him in place with her whole body as she eased the small dildo into his hole.

It hurt, even with all the prep and all the special, expensive lube, and he nearly called the whole thing off. She eased it in half way and stopped, waiting for him to make a decision; forward or out. When he nodded for her to go on, she waited another thirty seconds and he felt her move something around and a buzzing filled the air as Sam felt his hair stand on end.

“Oh fuck, oh fuck.” Jess whined from behind him and started pressing forward, unable to stop the way her hips rocked into the harness. He hadn’t even noticed that the whole thing vibrated but he could feel it in every nerve ending and pleasure center of his body.

“Yeah, yes, Jess.” His voice was so tight, it was agony forcing air through his throat to speak but he had to, had to call out, had to say her name. It was so good, so overwhelming, so all encompassing. He could already feel his orgasm tingling in his balls. He shoved his ass Backwards wanting that vibration closer to his body, inside of him even more than it already was, and the head of the dildo dragged across his prostate. 

Jess had only grazed it with her tiny fingers when she’d fingered him; this was so different that his vision whited out and he was coming, helpless to stop it, covering the sheets beneath him and clenching down around the toy so hard that he hurt himself.


End file.
